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by SyntheticSympathy
Summary: Little J fled the scene after the Kiss on the Lips party only to start a new life on the Upper West side. Now, at the middle of her sophomore year she's back and ready to prove that she's not so little anymore.
1. The Return of Little J

**Author's Note:**** To reduce confusion I would just like to say that Lily and Rufus are already engaged at this point rather than waiting until the end of the second season. Since Jenny wasn't there to tell on Chuck and Blair their relationship is still under wraps and Blair and Nate are still an 'item'. Blair is just as powerful as ever and still reigning undisputedly as Queen Bee, but not for long.**

**The Return of Little J**

Her chest rose and fell; the smooth porcelain skin swelling against the black confines of her bodice with each deep intake of air. The tip of her rosy pink tongue flashed across the parched crimson flesh of her plump lower lip as she second guessed her decision once more to crash the annual masquerade held by the one and only Blair Waldorf. Eyes of blue and gray steel sparkled with determination as she strode towards the back entrance, her designer stilettos clicking against the worn pavement of the Upper East Side with each graceful step. She smiled seductively at the scrawny excuse for a guard that blocked her way. Jenny Humphrey was completely adamant about getting inside the building and she wasn't above making some poor little sap squirm a bit to do so. After all, she had to prove that 'Little J' wasn't quite so little anymore.

It had been well over a year since she'd ran away from her freshman year at Constance Billard and the people she both loved and hated. It had been on the rooftop of the very building she stood before that her life had taken that fateful turn. He'd been so charming and she'd never been more naïve or hungry for the popularity she so desperately wanted. Jenny resisted the urge to sigh in frustration or throw the nearest object out of anger at her former self. If her brother hadn't shown up to save the day and throw a well-placed punch at the arrogant face of Chuck Bass the young blond wasn't sure where she'd be at the moment. She did know that neither her virginity nor her pride would still be intact. Jenny Humphrey had never been so thankful for having an elder brother then on that single night.

Rather than facing the devil himself, Jenny had fled to her mother's humble abode only be relocated to the Upper West Side once the divorce papers finally went through and her mother found a new husband in billionaire Sebastien Fatale. Entering into a top notch private school as the step-daughter of a prominent record label owner certainly had its advantages, but she still didn't have the world at her feet. Little Jenny Humphrey had turned into Queen J at her new school with extremely hard work and determination, and it was all thanks to Chuck Bass. Truth be told it was ironic, but if it weren't for that mother chucker she never would have opened her eyes or stopped being the lap dog to the higher ups. She would have continued to blindly follow the Blair Waldorf's of the world in hopes of being thrown the proverbial bone.

Time however had changed, and not only with herself but with the whole of the Upper East Side as well. The name Humphrey was enough to gain the young woman a rather ample amount of recognition within the upper levels of the world these days. Not because of power or fear but the money that went with her father's hopefully soon marriage to one Lily Van der Woodsen. Jenny had made it her mission to step out of the shadows of her past life and though this new marriage would make it easy, the young girl was determined to make a mark on the world without the help of anyone else. Her life wasn't a dream and it certainly wasn't easy...her life was hard work and careful planning. Every move she made had a reason and every thought a meaning. Jenny had fought hard to make herself the woman that she was, and she continued to fight to keep herself on the ground. Together with Eric –who she'd kept in touch with since leaving- she would work to take the throne from Blair and make the high school years bearable once more. It was a game to her and like every game there was a very clear and precise set of rules.

1. Never trust – it only leads to destruction.  
2. Never love – it only makes you weak.  
3. Don't let the game play you because once fallen you can't get up.

Though Jenny didn't believe in love she had learned to use the illusion to her advantage. It sickened her, the way couples pretended to be so happy, and the way their eyes found one another across a crowded room. It reminded her of the way his eyes had found hers from across the dimly lit dance floor. Jenny eased her nausea and disgust by bringing the male population to its knees with her wit and sexuality without ever once having to jump anyone's bones. There was only one thing about Jenny Humphrey these days that could ever be described as pure and innocent and that was her virginity; a small white fleck on her otherwise dark presence that wasn't about to go away. If anything her precious little flower was far too delicious of a weapon to give up to just anyone. To Jenny, love was simply an overused word that described nothing more than a pure animalistic lust for another person and a weakness to boot. It was a weakness best left out of her busy and ever winding path of life. There simply wasn't a use for it, and the young woman didn't have time to cater to its ever demanding needs. She did however have time to use lust for her own personal gain.

"Excuse me Miss," the scrawny little man piped up as she stepped closer, "but the entrance to the masque is in the other direction."

Jenny eyed her target, her crimson lips curling into a pleasant smile as she stood before him. He looked to be about twenty-two or so –probably someone who needed a little extra cash for college.

"Well," Jenny's voice lowered in a sultry whisper, her slender fingers wrapping gently around his shoulder, "I'm trying to surprise a couple of friends and you know these masks…always able to tell who's behind them anyway. If you'd just let me through the back here it would be so much easier for me to go by unnoticed."

She knew that no one would recognize her. Jenny had grown to an impressive 5' 7" and despite the impulse to cut it short and choppy the young woman had let her newly dyed platinum blond locks grow well past her shoulders. If anything she'd grown into quite the picture of beauty and womanhood during her time away.

"I'm really not supposed to," he finally replied, his eyes raking over her slender form.

"Well rules are meant to be broken," Jenny answered easily, her fingers moving to caress his jawline, "you know I always was a sucker for the bad boy."

He gulped as the midnight black nail of her index finger trailed along the main artery of his neck, his eyes widening as he let out short rapid breaths of air.

"Just this once," he said raggedly, "meet me after its over?"

"You can count on it," Jenny replied, smiling victoriously as she moved past the door that he had so graciously opened for her before whispering, "sucker." Jenny Humphrey had no intention of coming back when there was so much waiting for every step forward.

**"Enter stage left," **she whispered upon entering the throng of people,** "and don't fuck it up."**

**What's this, a party crasher on the Upper East Side? My, my, Queen B won't be so happy with this lady in black. Who are you mystery girl? I'll be sure to keep you posted.**

**XOXO**

**Gossip Girl**


	2. Get It Up

**Author's Note: **I would just like to say thank you to shadylady21 for being my first reviewer. I hope don't let you down! Also I don't own Gossip Girl or its characters, otherwise Chuck Bass would have a permanent vacation in my bedroom. Just saying. Also, this is the first time I've ever tried writing from Chuck's point of view so I can only hope I did him justice. Otherwise read and enjoy.

Jenny's Dress: [http]:/[www].polyvore.[com]/blah/set?id=[19030740]

Chuck's Suit: [http]:/[www].polyvore.[com]/cgi/thing?id=[16971086]

Just remove the brackets.

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**Get It Up**

Charles Bass, more commonly known as Chuck, liked to think that he was God's gift to women or even better still that women were God's gift to him. They were put on this earth for him to corrupt and degrade all in the name of a good –usually drunken- time. He could wallow in their supple flesh and pound into them until they were all bags of spent and unthinking bones. They were simply a trifle of sorts to take out his pain and depression. Yes, the man who had everything was depressed. He hadn't even known his mother until she showed up to unsuccessfully take away everything that he owned and his father was rotting six feet under. Now, what does someone give the person who has everything and nothing all at once? Should this person be Chuck Bass there is no better gift then the tinkling of glass and ice in the form of a nice stiff drink and the welcoming arms of that day's conquest.

Too bad Chuck Bass hadn't had the pleasures of anyone's flesh but Blair Waldorf's for little over a year and counting. In truth, it should have been the life. Chuck could easily drown in his lady's chocolate orbs for days on end, or at least he could if their little trysts weren't penciled in whenever Nathaniel Archibald wasn't around. At first it had been a rush. He'd taken the 'Queen's' virginity on top of the smooth polished leather interior of his limo with little thought to her boyfriend and his best friend. She had been a divine goddess in his eyes, a temptress after his own heart as she'd danced under the lights of the Victrola. It was then that he could see just how dangerous his Queen was when it came to matters of the heart; his own in particular. Their 'romance' had been a rush of fresh air that knocked him down and left him gasping for air. That was until the monotony of their fling had finally came calling. As time passes, what was once shiny and new dims a little and occasionally loses its value. The 'butterflies' as Blair had once called them had almost completely stopped fluttering and the adrenaline that came with the thrill of an affair had dried up to nothing but pure unadulterated boredom. Though he hated to admit it, there was a bit of disappointment as well.

Bass was second to none, and as far as he was concerned Blair should have left Nathaniel long ago. Not because they were in love –no, he wasn't capable of that- , but because Chuck Bass was…well, Chuck Bass. He wasn't meant to be hidden away like some dirty little secret…not unless there was some sort of fun involved. Chuck smiled lecherously at his reflection, his hands securing the black satin ties of his mask as he thought over the rut he'd become stuck in. Perhaps it was time to spice things up.

Chuck swirled drink in his hand, his eyes watching as the amber liquid churned within its glass confines. He knew without being told that he was dressed to impress; his suit a pure and virginal white minus the fine black borders around the lapels and cuffs of his jacket that matched his vest and the demon's mask resting upon his perfectly chiseled features. If the way Blair's eyes roamed over his body were any indication he had above and beyond exceeded expectations.

"See something you like?" His throaty whisper enveloped the brunette's ear in a rush of hot air that sent tingles through every nerve of her body.

Blair narrowed her eyes, stepping away from her own personal demon. It wouldn't do to be caught after the game had been played for so long. Things were rocky enough with her boyfriend anyway. What, was she supposed to not worry about newly single Serena? Sure, the sultry voiced blond was her best friend but that didn't change history. Blair was scared out of her mind.

"I was simply admiring the upholstery," she said finally, her voice even though slightly breathless in quality, "What is that, Armani?"

"Admiring the upholstery," he repeated, the corner of his lip curling into a signature smirk, "but Blair it's the interior that speaks for itself. I can simply imagine what you'd like out of that dress, or better yet on me. The things I could do to you." His arm had snaked around her waist, pulling her taught against his chest as he pressed a light fluttering kiss to her porcelain neck.

"You'd ravish me, I'm sure." Blair rolled her eyes, swatting him away as she pulled out of his grasp and quickly grabbed a flute of champagne from a passing waiter. "You can't keep doing this," she hissed, "not in public. Who do you think you are?"

"I'm Chuck Bass," he answered angrily, his hand grabbing onto her arm before she could run after Nate's coat tails for the rest of the night, "and you'd do best to remember that. I'm not going to wait around forever Waldorf."

Blair stared into his eyes, and she knew without a doubt that he was serious. She turned her head this way and that like a wild animal caught in a hunter's trap, but there was no one she could turn to. Not when Gossip Girl was always around and their situation HAD to be kept private.

"You wouldn't," she said finally, "you wouldn't just ruin your friendship like that."

"Try me Waldorf," he said finally, his gaze roaming around the room as he let go of her arm. A flash of sheer black and a wave of platinum hair had caught his eye. He smiled, his lips curling into a predatory leer as he stepped away from his 'Queen' without so much as a goodbye. Chuck Bass was tired of playing the domesticated boy toy and so help him if the front of that beauty was as delicious looking as the back not even a winter in hell would stop him from going back to his old devilish ways.

"Mother Chucker," Blair whispered under her breath, her mind filled with doubts and worries as she ran off in search of her longtime boyfriend.

In the meantime Chuck had found his goddess in black. His brown orbs raked up and down her body – twice for good measure. Her dress of sheer black clung to her in all the right places, the black sequins covering her for modesty's sake without looking tacky. It was her hair that drew most of his attention though; long platinum tendrils of hair that fell over one shoulder in a cascade of waves that simply screamed 'touch me'. Chuck smiled once more, promising himself that by the end of the night his hands would be buried in that mane of hair as she screamed his name in the throes of passion.

His lips caressed the porcelain knuckles of her right hand as he bent low in the most elegant of bows. Their eyes met, and electricity shot through the two of them until it seemed as if they were the only two people in the room. Chuck grinned, his tongue curling behind his teeth in a suggestive manner as he dared to ask, "Care to dance with the devil?"

**Spotted: Chuck Bass and the Lady in Black. Tell me C, is this another conquest or will you end up going home alone, and how does Queen B feel about you taking up with our mystery crasher? **

**You know you love me,**

**xoxo**

**Gossip Girl**


	3. Stamina

Sorry this is so late! I've been so busy with school and stuff its not even funny, but I've already started on the next chapter and it should be up by tonight. I promise...no more teasing with the chapters.

I don't own Gossip Girl, although I wish I did because the seasons would have gone completely different then they have. Reviews are loved, and make me happy.

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Hell, Jenny Humphrey was in Hell, population of two people. That simply had to be the answer. Some higher power, God, Allah, Buddah or whatever hated her guts and had chosen that exact moment in time to plunge her well past the seventh layer. Had she done something so terrible in a past life that Karma had to choose right then to play the bitch? Masked eyes of blue gray fell on the 'demon' standing before her, tracing the finely tailored lines of his suit before resting on the chocolate orbs that had haunted her for the better part of a year. There was no Dan to save her this time around, and as appealing running away from the entire situation was, Jenny simply couldn't back down now. Instead, the young blonde smiled, ignoring the spark of electricity that shot through her core as the devil himself pressed a fluttering kiss to the knuckles of her right hand.

"Care to dance with the Devil?"

His voice was smooth like honey, and just as warm and enticing as she remembered it. Jenny closed her eyes allowing a few seconds to savor in its deceiving sweetness before glancing over her 'partner' with a predatory grin.

"It depends," she replied in her own well practiced sultry whisper, "on whether or not you can keep up."

Chuck smirked, using his grip on her hand to pull her closer. Their chests touching as he gripped the small of her back in an almost intimate embrace. It was from this position that he twirled the young blonde onto the dance floor. He was glad that a faster song was playing, one that he could watch his mystery woman swing those lovely little hips to. He'd never been a fan of slow songs. They were usually too 'lovey dovey' and as far as he was concerned there was far too little invasion of personal space.

"I think I can keep it up," his voice was low and dangerously seductive as he flipped her around so her back was against his chest, "and still have the stamina for another round."

Jenny laughed at his ill hidden innuendo before letting the music take over. Their bodies fit well together, her arm draping back around his neck as easily as his arm found home on her thigh. Together they moved in time to the music, each too wrapped up in the other and their own individual plans to fully notice the seething Queen B angrily watching their every move. Jenny was lost, trying to find the perfect way to work this situation to her advantage and Chuck was too busy trying to find out how to get his Lady in Black out of her damned dress.

The arm not resting at Jenny's thigh slid down her ribcage; teasing the flesh underneath her dress with a faint trail of electricity that simply promised to be so much more if only she would let it. Her body slid down his toned frame; the curves of her body conforming to fit perfectly with his as she slid back up. Chuck groaned, flipping her around once more in a way that allowed her to feel the very thing that made him quite popular with the ladies. Her eyes widened, and just for a moment the brown haired boy was reminded of a darker blond fifteen year old from the year before. His mystery woman flipped away from him leaving him cold from the loss of her body heat, and all thoughts of the girl from Brooklyn fled away as she fell into him once more.

Finally the music ended, the two partners facing one another on the field once more. Their breathing was slightly labored, their chests almost rising and falling in unison as they moved away from the dance floor. Chuck grabbed two flutes of champagne from a passing waiter before handing one to his companion.

"Tell me," he said finally, "did I live up to your expectations?"

Jenny smiled, sipping from her glass before moving closer to the dark knight of her worst dreams. She placed her hand on his chest, well manicured fingers tracing circles in the luxurious material of his suit.

"Impressive," the blonde chose her words carefully, uttering each syllable with the same level seduction, "but I'd hardly call that a full performance."

Chuck Bass bristled at the hidden jab at the quality of his work, his eyes narrowing ever so slightly as he took in the mischievous expression in the blonde's eyes. He looked down at the hand on his chest, his lips curving into a seductive smile as he stared at her from between thick lashes that should be forbidden for any man.

"And how," he whispered, his breath hot against her neck as he leaned towards her, "do we begin to remedy that?"

Jenny simply smiled, her hand grasping his as she led him towards the rooftop that haunted her memories.

**What's this, C on the rooftop again? Let's hope he doesn't leave with a black eye this time around, but looking at B you never know.**

**xoxo Gossip Girl**


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